Acetyl chloride → HCID 10686612, compound

Participants

Reaction Steps

A solution of 4-amino-7-chloro-3-phenyl-2(1H)-quinolone (Example 2) (0.3 g) in tetrahydrofuran (30 ml) was treated with sodium hydride (0.2 g, 80% disp. in oil). After 1 h, acetyl chloride (0.7 ml) was added and the reaction mixture was stirred for 2 h at room temperature then heated under reflux for 14 h. The reaction was partitioned between water and ethyl acetate. The organic phase was dried (MgSO4) and the solvent was removed in vacuo. The residue was suspended in 1N NaOH, and placed in an ultrasound bath for 5 mins. The aqueous phase was extracted with diethyl ether, acidified to pill and the precipitate produced was collected by filtration to give the title compound (0.080 g); mp 275°-277° C. (DMF-water). Found: C, 58.39; H, 4.83; N, 8.02. C17H13ClN2O2.2H2O requires C, 58.54; H, 4.91; N, 8.03%; δ (360 MHz, DMSO-d6) 1.88 (3H, s, CH3CO), 7.22-7.58 (8H, m, aromatics), 9.69 (1H, br s, NH), 12.06 (1H, br s, NH); m/z (EI) 312 (M+).

Provenance & Evidence